Hydrochloric Acid → HCID 21105742, compound

HRID 1354466Notes

Reaction equation

HRID 1354466 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[C:14]1[O:18][N:17]=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[N:15]=1)[C:7]([O:9]C)=[O:8])([O-:3])=[O:2].[OH-].[Na+].Cl>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[C:14]1[O:18][N:17]=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[N:15]=1)[C:7]([OH:9])=[O:8])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22934541HCID 22934541, compound

Product 1

HCID 21105742HCID 21105742, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3-nitro-4-[3-(4-trifluoromethylphenyl)-1,2,4-oxadiazol-5-yl]benzoate (2.00 g), 1 M aqueous sodium hydroxide solution (10.2 ml) and tetrahydrofuran (10 ml) was heated under reflux for 1 hr. After cooling, 1 M hydrochloric acid was added to acidify the reaction mixture. The crystals were collected by filtration to give 3-nitro-4-[3-(4-trifluoromethylphenyl)-1,2,4-oxadiazol-5-yl]benzoic acid (1.84 g, yield 95%). Recrystallization from hexane-tetrahydrofuran gave pale-yellow prism crystals. melting point: 233–234° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hr
  3. temperatureAfter cooling
  4. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-4f9c0e90b51b4110b0b2944a14c1752f
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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